US10251858B1 - Composition for treating fungal infections in nails - Google Patents

Composition for treating fungal infections in nails Download PDF

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US10251858B1
US10251858B1 US15/671,719 US201715671719A US10251858B1 US 10251858 B1 US10251858 B1 US 10251858B1 US 201715671719 A US201715671719 A US 201715671719A US 10251858 B1 US10251858 B1 US 10251858B1
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acid
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composition
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Perry Forrester
Joshua Scott
James Adkinson
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Marlinz Pharma LLC
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Marlinz Pharma LLC
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    • A61K31/325—Carbamic acids; Thiocarbamic acids; Anhydrides or salts thereof
    • A—HUMAN NECESSITIES
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    • A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
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    • A61K36/18—Magnoliophyta (angiosperms)
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    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
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    • A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
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    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
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Definitions

  • the present invention relates to a composition for use in the topical treatment of nails, e.g., finger nails and toe nails. More particularly, the present invention relates to a composition for treating nails and surrounding tissue affected by or susceptible to fungal infections.
  • compositions used to treat nails of an individual for cosmetics purposes, therapeutic purposes, preventative purposes, or all of the above are common and there are numerous, commercially available topical preparations to treat these fungal infections.
  • compositions for treating nail fungal infections typically contain a large proportion of oil.
  • the prior art compositions typically contain oils, principally of vegetable origin, which are also used in a wide variety of cosmetic products.
  • these cosmetic oils are composed principally of saponifiable esters, particularly fatty acid tryglycerides.
  • Non-limiting examples of such vegetable oils include soybean oil, avocado oil, corn oil, sesame oil, sunflower oil, almond oil, etc. It is also known to use oils and fats derived from animals such as mink oil, and beef tallow.
  • the compositions typically contain a preservative or antioxidant as for example parabens, i.e., esters of parahydroxybenzoic acid, the most common being methyl paraben, propyl paraben, and butyl paraben.
  • a preservative or antioxidant as for example parabens, i.e., esters of parahydroxybenzoic acid, the most common being methyl paraben, propyl paraben, and butyl paraben.
  • antioxidants such as butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT) have also been used as preservatives/antioxidants.
  • the present invention relates to a topical preparation to treat certain nail disorders.
  • the present invention relates to a composition for treating nail fungus.
  • the present invention relates to a composition for treating nail fungus which requires no preservatives or antioxidants for stability.
  • the present invention relates to an antifungal composition for topical use on the nails which uses a minor amount of oil having a high oxidative stability index.
  • nail or “nails” means one or more of the toe nails and/or finger nails of an animal, particularly humans.
  • the basic composition of the present invention comprises a urea-based component, a monohydric alcohol, a diol, undecylenic acid, a carboxylic acid other than undecylenic acid, dimethyl isosorbide, and O-2-naphthyl methyl(3-methylphenyl)thiocarbamate (tolnaftate).
  • urea-based component is urea itself
  • a urea-based component can comprise urea peroxide or carbamide peroxide. It is known that these urea-based components serve a cosmetic function in that they improve the visual appearance of the nail thereby providing an incentive for the user to be diligent in applying the composition, a necessity to eradicate fungal infections. Urea-based components also act as a nail penetrator and/or softener.
  • the urea component will be present in the composition in an amount of from about 2 to about 15% by weight, preferably from about 2 to about 6% by weight, where all percentages stated herein are by weight of the total composition.
  • compositions of the present invention comprise a monohydric alcohol containing from 2 to 4 carbon atoms, the alcohol being present in an amount of from about 10 to about 55% by weight, preferably from about 15 to about 30% by weight.
  • the monohydric alcohol can be ethanol, propanol, isopropanol, etc., isopropanol being preferred.
  • the composition can contain up to about 7% water.
  • compositions of the present invention also contain a carboxylic acid component other than undecylenic acid.
  • the carboxylic acid component comprises a C1 to C10 organic acid which can be alone and/or in an aqueous solution and is present in the composition in an amount of from about 10 to 25% by weight, preferably from about 10 to 15% by weight.
  • C1-C10 carboxylic acids suitable for use in the composition of the present invention include saturated and/or unsaturated, linear and/or branched, aliphatic mono-, di-, carboxylic acids, alkylaryl or aromatic dicarboxylic acids, oxy- and hydroxyl-carboxylic acids (e.g., alpha-hydroxy acids).
  • Preferred carboxylic acids include formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, capyric acid, capric acid, sorbic acid, oxalic acid, hydroxybutyric acid, hydroxypropionic acids, lactic acid, glycolic acid, citric acid, malic acid, tartaric acid, malonic acid, fumaric acid, succinic acid, glutaric acid, apidic acid, pimelic acid, oxalacetic acid, phthalic acid, tartronic acid, pyruvic acid, and mixtures thereof.
  • An especially preferred carboxylic acid is lactic acid.
  • compositions of the present invention can also contain from about 2 to about 10% by weight, preferably from about 2 to about 6% by weight, of a carboxylic acid ester having the formula:
  • R 1 comprises 1 to 3 carbon atoms
  • R 2 comprises 2 to 4 carbon atoms.
  • suitable ester examples include methyl acetate, ethyl acetate, methyl propionate, etc., ethyl acetate being preferred.
  • undecylenic acid (undec-10-enoic acid), an unsaturated fatty acid. While not wanting to be bound by any particular theory, it is believed that undecylenic acid acts as an emulsifier and also perhaps as a linking agent which brings certain components of the composition of the present invention together to form a clear, stable solution. It is also believed that undecylenic acid can act as a biocide/antimicrobial to some extent and thereby enhance the stability of the compositions of the present invention. Undeclyenic acid has the additional benefit that, in and of itself, it possesses antifungal properties thereby enhancing the efficacy of the compositions of the present invention in treating fungus as well as other nail infections. The undecylenic acid will be present in the composition of the present invention in an amount of from about 15 to about 30% by weight, preferably from about 20 to about 30% by weight.
  • the antifungal used in the composition of the present invention is tolnaftate.
  • the tolnaftate will generally be present in the composition in an amount of from about 0.3 to about 5% by weight, preferably from about 0.3 to about 3% by weight.
  • the antifungal compositions of the present invention can include other components which can function in one of several ways such as imparting solubility to render the composition a stable solution, imparting therapeutic benefits, imparting aesthetic effects or enhancing ease of application of the composition to the nails.
  • DMI dimethyl isosorbide
  • the DMI will be present in the composition of the present invention in an amount of from about 8 to about 20%, preferably from about 8 to about 15%, by weight.
  • One of the additional components that can be employed is an ester of a fatty acid.
  • the fatty acid esters can have the formula:
  • R 3 comprises 10 to 22 carbon atoms.
  • Non-limiting examples of suitable fatty acid esters are esters of caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, and behenic acid.
  • the ethyl, methyl, propyl, and/or isopropyl esters of these fatty acids can be employed, a preferred fatty acid ester being isopropyl myristate.
  • the fatty acid ester will be present in an amount of from about 2 to about 10% by weight, preferably from about 2 to about 6% by weight.
  • the composition of the present invention can also include a diol containing from about 2 to about 4 carbon atoms.
  • suitable diols include ethylene glycol, propylene glycol, etc.
  • a preferred diol is propylene glycol.
  • the diol will generally be present in an amount of from about 4 to about 15% by weight, preferably from about 4 to about 10% by weight.
  • compositions of the present invention can also include with advantage jojoba oil.
  • Jojoba oil is comprised mostly of free fatty acids and is characterized by its long shelf life as compared to other vegetable oils, primarily because it has no triglycerides. In this regard, it has an oxidative stability index of 60 as determined by AOCS standard method CD12b-92.
  • the jojoba oil will be present in the composition in an amount of from about 1 to about 10% by weight, preferably from about 1 to about 5% by weight.
  • compositions of the present invention can contain vitamin E in an amount of from about 0.5 to about 10% by weight, preferably from about 0.5 to about 3% by weight.
  • a desired form of vitamin E is vitamin E acetate having the formula C 31 H 52 O 3 .
  • Vitamin E acetate is commonly referred to as tocopherol acetate and is also known as DL- ⁇ -Tocoferil Acetate; (+/ ⁇ )- ⁇ -Tocopherol Acetate; and DL-a-Tocopheryl Acetate.
  • Vitamin E suitable for use in the compositions of the present invention is available from Spectrum Chemical Manufacture Corp. under the product code VI140, product name Vitamin E Acetate, USP.
  • An especially useful composition according to the present invention is one consisting essentially of 0.5 to 3% by weight tolnaftate, 2 to 6% by weight urea, 10 to 15% by weight lactic acid, 2 to 30% by weight undecylenic acid, 8 to 20% by weight DMI, 4 to 15% by weight propylene glycol, and 15 to 50% by weight isopropyl alcohol. Formulations containing these components showed the ability to rapidly eliminate fungal infections in toe nails.
  • An antifungal composition was prepared by mixing 3 grams of urea, 12.06 grams of lactic acid, 22.8 grams of undecylenic acid, 1 gram of tolnaftate, 4.5 grams of ethyl acetate, and 44.7 grams of isopropanol. The mixture was stirred in a beaker at a temperature of 55° C. until the mixture formed a clear solution. Upon cooling, no settling was observed. It was found that the composition could be applied to nails without leaving any significant waxy/oily surface residue.
  • a composition was prepared by combining 3 grams of urea, 23.58 grams of isopropanol, 4.25 grams of isopropyl myristate, 12.06 grams of lactic acid, 22.8 grams of undecylenic acid, 1 gram of tolnaftate, 4.49 grams ethyl acetate, 6.94 grams jojoba oil, 7.6 grams vitamin E, and 6.24 grams of propylene glycol.
  • the mixture was stirred in a beaker at a temperature of 55° C. until a clear solution was formed. Upon cooling, no settling was observed. It was found that the composition thus prepared could be applied to nails without leaving any significant amount of oil/waxy surface residue.
  • An antifungal composition was prepared which contained about 1.06 wt % tolnaftate, about 4.76 wt % ethyl acetate, about 4.51 wt % isopropyl myristate, about 3.18 wt % urea, about 21.67 wt % isopropyl alcohol, about 2.74 wt % jojoba oil, about 1.01 wt % vitamin E, about 6.61 wt % propylene glycol, about 12.80 wt % lactic acid, about 24.17 wt % undecylenic acid, about 12.19 wt % dimethyl isosorbide, and about 5.30 wt % purified water.
  • the thus prepared antifungal composition was applied to two patients suffering severe toenail fungus. Markedly visible results in terms of reduced discoloration were seen in as little as ten days with respect to both patients. Additionally, after four weeks of treatment, it was found that there was marked improvement in the toenails of both patients.
  • An antifungal composition containing 3.3% by weight, 13.2% by weight lactic acid, 25.0% by weight undecylenic acid, 12.6% by weight dimethyl isosorbide, 6.8% by weight propylene glycol, 1.0% by weight tolnaftate, and 38.0$ by weight isopropyl alcohol was prepared by mixing the ingredients together at room temperature until a clear solution was formed.
  • compositions prepared according to Examples 1, 2, 3, and 4 were found to undergo no degradation or settling after remaining quiescent at room temperature for 3 months. In this regard, no discoloring or rancid odor of the composition was observed. This indicates that the compositions are stable, albeit that they contain no commonly used preservatives and/or antioxidants as discussed above, e.g., parabens.
  • nail polish can be applied with good adherence.

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Abstract

A pharmaceutically active composition suitable for topical application to the nails contains undecylenic acid and tolnaftate. The composition also employs a urea-based component, a monohydric alcohol such as isopropanol, a diol such as propylene glycol, dimethyl isosorbide, and a carboxylic acid other than undecylenic acid, preferably lactic acid.

Description

CROSS REFERENCE TO RELATED APPLICATION
This application claims priority to U.S. Application No. 62/372,132 filed on Aug. 8, 2016, the disclosure of which is incorporated herein by reference for all purposes.
FIELD OF THE INVENTION
The present invention relates to a composition for use in the topical treatment of nails, e.g., finger nails and toe nails. More particularly, the present invention relates to a composition for treating nails and surrounding tissue affected by or susceptible to fungal infections.
BACKGROUND OF THE INVENTION
The prior art abounds with compositions used to treat nails of an individual for cosmetics purposes, therapeutic purposes, preventative purposes, or all of the above. In particular, fungal infections of various types of the nails, particularly toe nails, are common and there are numerous, commercially available topical preparations to treat these fungal infections.
One disadvantage of many commercially available compositions for treating nail fungal infections, be they over-the-counter or proprietary, is that the compositions typically contain a large proportion of oil. Thus, the prior art compositions typically contain oils, principally of vegetable origin, which are also used in a wide variety of cosmetic products. As is known, these cosmetic oils are composed principally of saponifiable esters, particularly fatty acid tryglycerides. Non-limiting examples of such vegetable oils include soybean oil, avocado oil, corn oil, sesame oil, sunflower oil, almond oil, etc. It is also known to use oils and fats derived from animals such as mink oil, and beef tallow.
Antifungal compositions containing a high proportion of oils and fats, be they vegetable or animal, suffer from several disadvantages. For one, because these oils are prone to degradation, the compositions typically contain a preservative or antioxidant as for example parabens, i.e., esters of parahydroxybenzoic acid, the most common being methyl paraben, propyl paraben, and butyl paraben. In addition, antioxidants such as butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT) have also been used as preservatives/antioxidants. While there is no unassailable evidence that the preservatives/antioxidants pose any serious health risks, many people are wary of their potential health risks and in general seek to avoid compositions which contain them. This can become a problem if they are present in nail antifungals since the patient may be reluctant to use the nail antifungal with the frequency required to eliminate the fungal infection.
Another disadvantage of antifungal formulations containing high amounts of oils or fats is that they leave a deposit on the nail surface which can be unpleasant for the user, and can also result in poor adherence of nail polish or the like to the nail surface. While this is a cosmetic issue, it is nonetheless a nuisance.
SUMMARY OF THE INVENTION
In one aspect, the present invention relates to a topical preparation to treat certain nail disorders.
In another aspect, the present invention relates to a composition for treating nail fungus.
In yet another aspect, the present invention relates to a composition for treating nail fungus which requires no preservatives or antioxidants for stability.
In yet a further aspect, the present invention relates to an antifungal composition for topical use on the nails which uses a minor amount of oil having a high oxidative stability index.
These and further features and advantages of the present invention will become apparent from the following detailed description, wherein reference is made to the FIGURES in the accompanying drawings.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
As used herein, the terms “nail” or “nails” means one or more of the toe nails and/or finger nails of an animal, particularly humans.
The basic composition of the present invention comprises a urea-based component, a monohydric alcohol, a diol, undecylenic acid, a carboxylic acid other than undecylenic acid, dimethyl isosorbide, and O-2-naphthyl methyl(3-methylphenyl)thiocarbamate (tolnaftate).
Although the preferred urea-based component is urea itself, a urea-based component can comprise urea peroxide or carbamide peroxide. It is known that these urea-based components serve a cosmetic function in that they improve the visual appearance of the nail thereby providing an incentive for the user to be diligent in applying the composition, a necessity to eradicate fungal infections. Urea-based components also act as a nail penetrator and/or softener. The urea component will be present in the composition in an amount of from about 2 to about 15% by weight, preferably from about 2 to about 6% by weight, where all percentages stated herein are by weight of the total composition.
In addition to the urea-based component, the compositions of the present invention comprise a monohydric alcohol containing from 2 to 4 carbon atoms, the alcohol being present in an amount of from about 10 to about 55% by weight, preferably from about 15 to about 30% by weight. The monohydric alcohol can be ethanol, propanol, isopropanol, etc., isopropanol being preferred. Optionally, the composition can contain up to about 7% water.
Compositions of the present invention also contain a carboxylic acid component other than undecylenic acid. Generally speaking, the carboxylic acid component comprises a C1 to C10 organic acid which can be alone and/or in an aqueous solution and is present in the composition in an amount of from about 10 to 25% by weight, preferably from about 10 to 15% by weight. Non-limiting examples of C1-C10 carboxylic acids suitable for use in the composition of the present invention include saturated and/or unsaturated, linear and/or branched, aliphatic mono-, di-, carboxylic acids, alkylaryl or aromatic dicarboxylic acids, oxy- and hydroxyl-carboxylic acids (e.g., alpha-hydroxy acids). Preferred carboxylic acids include formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, capyric acid, capric acid, sorbic acid, oxalic acid, hydroxybutyric acid, hydroxypropionic acids, lactic acid, glycolic acid, citric acid, malic acid, tartaric acid, malonic acid, fumaric acid, succinic acid, glutaric acid, apidic acid, pimelic acid, oxalacetic acid, phthalic acid, tartronic acid, pyruvic acid, and mixtures thereof. An especially preferred carboxylic acid is lactic acid.
The compositions of the present invention can also contain from about 2 to about 10% by weight, preferably from about 2 to about 6% by weight, of a carboxylic acid ester having the formula:
Figure US10251858-20190409-C00001
wherein R1 comprises 1 to 3 carbon atoms, and R2 comprises 2 to 4 carbon atoms. Non-limiting suitable ester examples include methyl acetate, ethyl acetate, methyl propionate, etc., ethyl acetate being preferred.
One of the primary ingredients used in the compositions of the present invention is undecylenic acid (undec-10-enoic acid), an unsaturated fatty acid. While not wanting to be bound by any particular theory, it is believed that undecylenic acid acts as an emulsifier and also perhaps as a linking agent which brings certain components of the composition of the present invention together to form a clear, stable solution. It is also believed that undecylenic acid can act as a biocide/antimicrobial to some extent and thereby enhance the stability of the compositions of the present invention. Undeclyenic acid has the additional benefit that, in and of itself, it possesses antifungal properties thereby enhancing the efficacy of the compositions of the present invention in treating fungus as well as other nail infections. The undecylenic acid will be present in the composition of the present invention in an amount of from about 15 to about 30% by weight, preferably from about 20 to about 30% by weight.
The antifungal used in the composition of the present invention is tolnaftate. The tolnaftate will generally be present in the composition in an amount of from about 0.3 to about 5% by weight, preferably from about 0.3 to about 3% by weight.
In addition to the above components, the antifungal compositions of the present invention can include other components which can function in one of several ways such as imparting solubility to render the composition a stable solution, imparting therapeutic benefits, imparting aesthetic effects or enhancing ease of application of the composition to the nails. Advantageously, and especially desirable as a solvent for use in the compositions of the present invention, is dimethyl isosorbide (DMI). The DMI will be present in the composition of the present invention in an amount of from about 8 to about 20%, preferably from about 8 to about 15%, by weight.
One of the additional components that can be employed is an ester of a fatty acid. Specifically, the fatty acid esters can have the formula:
Figure US10251858-20190409-C00002
wherein R3 comprises 10 to 22 carbon atoms.
Non-limiting examples of suitable fatty acid esters are esters of caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, and behenic acid. In particular, the ethyl, methyl, propyl, and/or isopropyl esters of these fatty acids can be employed, a preferred fatty acid ester being isopropyl myristate. When employed, the fatty acid ester will be present in an amount of from about 2 to about 10% by weight, preferably from about 2 to about 6% by weight.
To ensure mutual solubility of the components and enhance stability, the composition of the present invention can also include a diol containing from about 2 to about 4 carbon atoms. Non-limiting examples of suitable diols include ethylene glycol, propylene glycol, etc. A preferred diol is propylene glycol. The diol will generally be present in an amount of from about 4 to about 15% by weight, preferably from about 4 to about 10% by weight.
The compositions of the present invention, can also include with advantage jojoba oil. Jojoba oil is comprised mostly of free fatty acids and is characterized by its long shelf life as compared to other vegetable oils, primarily because it has no triglycerides. In this regard, it has an oxidative stability index of 60 as determined by AOCS standard method CD12b-92. When used, the jojoba oil will be present in the composition in an amount of from about 1 to about 10% by weight, preferably from about 1 to about 5% by weight.
Advantageously, the compositions of the present invention can contain vitamin E in an amount of from about 0.5 to about 10% by weight, preferably from about 0.5 to about 3% by weight. A desired form of vitamin E is vitamin E acetate having the formula C31H52O3. Vitamin E acetate is commonly referred to as tocopherol acetate and is also known as DL-α-Tocoferil Acetate; (+/−)-α-Tocopherol Acetate; and DL-a-Tocopheryl Acetate. Vitamin E suitable for use in the compositions of the present invention is available from Spectrum Chemical Manufacture Corp. under the product code VI140, product name Vitamin E Acetate, USP.
An especially useful composition according to the present invention is one consisting essentially of 0.5 to 3% by weight tolnaftate, 2 to 6% by weight urea, 10 to 15% by weight lactic acid, 2 to 30% by weight undecylenic acid, 8 to 20% by weight DMI, 4 to 15% by weight propylene glycol, and 15 to 50% by weight isopropyl alcohol. Formulations containing these components showed the ability to rapidly eliminate fungal infections in toe nails.
To further demonstrate the invention, the following non-limiting examples are presented:
Example 1
An antifungal composition was prepared by mixing 3 grams of urea, 12.06 grams of lactic acid, 22.8 grams of undecylenic acid, 1 gram of tolnaftate, 4.5 grams of ethyl acetate, and 44.7 grams of isopropanol. The mixture was stirred in a beaker at a temperature of 55° C. until the mixture formed a clear solution. Upon cooling, no settling was observed. It was found that the composition could be applied to nails without leaving any significant waxy/oily surface residue.
Example 2
A composition was prepared by combining 3 grams of urea, 23.58 grams of isopropanol, 4.25 grams of isopropyl myristate, 12.06 grams of lactic acid, 22.8 grams of undecylenic acid, 1 gram of tolnaftate, 4.49 grams ethyl acetate, 6.94 grams jojoba oil, 7.6 grams vitamin E, and 6.24 grams of propylene glycol. The mixture was stirred in a beaker at a temperature of 55° C. until a clear solution was formed. Upon cooling, no settling was observed. It was found that the composition thus prepared could be applied to nails without leaving any significant amount of oil/waxy surface residue.
Example 3
An antifungal composition was prepared which contained about 1.06 wt % tolnaftate, about 4.76 wt % ethyl acetate, about 4.51 wt % isopropyl myristate, about 3.18 wt % urea, about 21.67 wt % isopropyl alcohol, about 2.74 wt % jojoba oil, about 1.01 wt % vitamin E, about 6.61 wt % propylene glycol, about 12.80 wt % lactic acid, about 24.17 wt % undecylenic acid, about 12.19 wt % dimethyl isosorbide, and about 5.30 wt % purified water. The thus prepared antifungal composition was applied to two patients suffering severe toenail fungus. Markedly visible results in terms of reduced discoloration were seen in as little as ten days with respect to both patients. Additionally, after four weeks of treatment, it was found that there was marked improvement in the toenails of both patients.
Example 4
An antifungal composition containing 3.3% by weight, 13.2% by weight lactic acid, 25.0% by weight undecylenic acid, 12.6% by weight dimethyl isosorbide, 6.8% by weight propylene glycol, 1.0% by weight tolnaftate, and 38.0$ by weight isopropyl alcohol was prepared by mixing the ingredients together at room temperature until a clear solution was formed.
The compositions prepared according to Examples 1, 2, 3, and 4 were found to undergo no degradation or settling after remaining quiescent at room temperature for 3 months. In this regard, no discoloring or rancid odor of the composition was observed. This indicates that the compositions are stable, albeit that they contain no commonly used preservatives and/or antioxidants as discussed above, e.g., parabens.
Further, since the treated nail surfaces are substantially free of any oil or waxy residue, nail polish can be applied with good adherence.
Although specific embodiments of the invention have been described herein in some detail, this has been done solely for the purposes of explaining the various aspects of the invention, and is not intended to limit the scope of the invention as defined in the claims which follow. Those skilled in the art will understand that the embodiment shown and described is exemplary, and various other substitutions, alterations and modifications, including but not limited to those design alternatives specifically discussed herein, may be made in the practice of the invention without departing from its scope.

Claims (13)

What is claimed is:
1. A pharmaceutically active composition suitable for topical application to the nails, comprising:
from about 2 to about 15% by weight of a urea-based component;
from about 10 to about 55% by weight of a monohydric alcohol containing 2 to 4 carbon atoms;
from about 8 to about 20% by weight of dimethyl isosorbide;
from about 15 to about 30% by weight of undecylenic acid;
from about 10 to about 25% by weight of a carboxylic acid component other than undecylenic acid;
from about 0.3 to about 5% by weight of O-2-naphthyl methyl(3-methylphenyl) thiocarbamate; and
from about 4 to about 15% by weight of a diol containing 2 to 4 carbon atoms.
2. The composition of claim 1, further comprising:
from about 1 to about 10% by weight jojoba oil.
3. The composition of claim 1, further comprising:
from about 0.5 to about 10% by weight Vitamin E.
4. The composition of claim 1, further comprising:
from about 2 to about 10% by weight of a carboxylic acid ester having the formula:
Figure US10251858-20190409-C00003
wherein R1 comprises 1 to 3 carbon atoms, and R2 comprises 2 to 4 carbon atoms.
5. The composition of claim 1, further comprising:
from about 2 to about 10% by weight of a fatty acid ester having the formula
Figure US10251858-20190409-C00004
wherein R1 comprises 1 to 3 carbon atoms, and R3 comprises 10 to 22 carbon atoms.
6. The composition of claim 1, wherein said urea-based component is present in an amount of from about 2 to about 6% by weight, said monohydric alcohol is present in an amount of from about 15 to about 30% by weight, said carboxylic acid component is present in an amount of from about 10 to about 15% by weight, said undecylenic acid is present in an amount of from about 20 to about 30% by weight, said dimethyl isosorbide is present in an amount of from about 8 to about 20% by weight, and said O-2-naphthyl methyl(3-methylphenyl)thiocarbamate is present in an amount of from about 0.3 to about 3% by weight.
7. The composition of claim 1, wherein said urea-based component comprises urea.
8. The composition of claim 1, wherein said monohydric alcohol comprises isopropyl alcohol.
9. The composition of claim 1, wherein said carboxylic acid component is selected from the group consisting of formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, capyric acid, capric acid, sorbic acid, oxalic acid, hydroxybutyric acid, hydroxypropionic acids, lactic acid, glycolic acid, citric acid, malic acid, tartaric acid, malonic acid, fumaric acid, succinic acid, glutaric acid, apidic acid, pimelic acid, oxalacetic acid, phthalic acid, tartronic acid, pyruvic acid, and mixtures thereof.
10. The composition of claim 9, wherein said carboxylic acid comprises lactic acid.
11. The composition of claim 5, wherein said fatty acid ester comprises isopropyl myristate in an amount of from about 2 to about 10% by weight.
12. The composition of claim 1, wherein said diol comprises propylene glycol in an amount of from about 4 to about 10% by weight.
13. An antifungal composition consisting essentially of 0.5 to 3% by weight tolnaftate, 2 to 6% by weight urea, 10 to 15% by weight lactic acid, 2 to 30% by weight undecylenic acid, 8 to 20% by weight dimethyl isosorbide, 4 to 15% by weight propylene glycol, and 15 to 50% by weight isopropyl alcohol.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022006508A1 (en) * 2020-07-02 2022-01-06 The Trustees Of Columbia University In The City Of New York Stable botanical antimicrobial compositions
WO2022006507A1 (en) * 2020-07-02 2022-01-06 The Trustees Of Columbia University In The City Of New York Stable botanical antimicrobial compositions

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10959975B1 (en) 2017-11-02 2021-03-30 The Tetra Corporation Antifungal composition, method of making composition, and method of using composition
CA3122016A1 (en) * 2018-12-19 2020-06-25 Marlinz Pharma, LLC Topical compositions

Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4810498A (en) 1986-02-13 1989-03-07 The Peau Corporation Nail oil composition
US5519059A (en) 1994-08-17 1996-05-21 Sawaya; Assad S. Antifungal formulation
US5525635A (en) 1986-02-04 1996-06-11 Moberg; Sven Pharmaceutical compositions containing propylene glycol and/or polyethylene glycol and urea as active main components and use thereof
US6391879B1 (en) 1998-11-16 2002-05-21 Astan, Inc. Therapeutic anti-fungal nail preparation
US7074392B1 (en) 2000-03-27 2006-07-11 Taro Pharmaceutical Industries Limited Controllled delivery system of antifungal and keratolytic agents for local treatment of fungal infections
US7374772B2 (en) 2002-11-07 2008-05-20 Bommarito Alexander A Topical antifungal treatment
US20110207765A1 (en) 2008-10-31 2011-08-25 Moberg Derma Ab Topical composition comprising a combination of at least two penetration enhancing agents
US20120010227A1 (en) 2009-07-30 2012-01-12 Technische Universitat Braunschweig Formulation for nail and nail bed diseases
US20120129942A1 (en) 2009-08-13 2012-05-24 Moberg Derma Ab Compositions and methods for treating fungal infection of the nail
US8333981B2 (en) 2007-10-09 2012-12-18 Humco Holding Group, Inc. Antifungal treatment of nails
US8952070B2 (en) 2011-02-11 2015-02-10 Moberg Pharma Ab Antifungal composition
US8987330B2 (en) 2013-03-15 2015-03-24 Moberg Pharma Ab Pharmaceutical composition for the treatment of fungal infections
US20170258917A1 (en) 2016-03-13 2017-09-14 Sevengenes Inc Solubility of therapeutic agents

Patent Citations (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5525635A (en) 1986-02-04 1996-06-11 Moberg; Sven Pharmaceutical compositions containing propylene glycol and/or polyethylene glycol and urea as active main components and use thereof
US4810498A (en) 1986-02-13 1989-03-07 The Peau Corporation Nail oil composition
US5519059A (en) 1994-08-17 1996-05-21 Sawaya; Assad S. Antifungal formulation
US6391879B1 (en) 1998-11-16 2002-05-21 Astan, Inc. Therapeutic anti-fungal nail preparation
US7074392B1 (en) 2000-03-27 2006-07-11 Taro Pharmaceutical Industries Limited Controllled delivery system of antifungal and keratolytic agents for local treatment of fungal infections
US7374772B2 (en) 2002-11-07 2008-05-20 Bommarito Alexander A Topical antifungal treatment
US8333981B2 (en) 2007-10-09 2012-12-18 Humco Holding Group, Inc. Antifungal treatment of nails
US20110207765A1 (en) 2008-10-31 2011-08-25 Moberg Derma Ab Topical composition comprising a combination of at least two penetration enhancing agents
US20120010227A1 (en) 2009-07-30 2012-01-12 Technische Universitat Braunschweig Formulation for nail and nail bed diseases
US20120129942A1 (en) 2009-08-13 2012-05-24 Moberg Derma Ab Compositions and methods for treating fungal infection of the nail
US8952070B2 (en) 2011-02-11 2015-02-10 Moberg Pharma Ab Antifungal composition
US9561279B2 (en) 2011-02-11 2017-02-07 Moberg Pharma Ab Antifungal composition
US8987330B2 (en) 2013-03-15 2015-03-24 Moberg Pharma Ab Pharmaceutical composition for the treatment of fungal infections
US20150306052A1 (en) 2013-03-15 2015-10-29 Moberg Pharma Ab Pharmaceutical composition for the treatment of fungal infections
US9782372B2 (en) 2013-03-15 2017-10-10 Moberg Pharma Ab Pharmaceutical composition for the treatment of fungal infections
US20170258917A1 (en) 2016-03-13 2017-09-14 Sevengenes Inc Solubility of therapeutic agents

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
Crawford, et al., Topical Treaments for Fungal Infections of the Skin and Nails of the Foot, The Cochrane Collaboration, 1999, Issue 3.
Faergemann, et al., Early and Visible Improvements after Application K101 in the Appearance of Nails . . . , J. of Cosmetics, 2011, 1 , 59-63.
podiatrynetwork.com, Topical Treatment for Fungal Toenails, www.podiatrynetwork.com/document_disorders.cfm?id=313, accessed Jul. 14, 2016.

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022006508A1 (en) * 2020-07-02 2022-01-06 The Trustees Of Columbia University In The City Of New York Stable botanical antimicrobial compositions
WO2022006507A1 (en) * 2020-07-02 2022-01-06 The Trustees Of Columbia University In The City Of New York Stable botanical antimicrobial compositions

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